Antimicrobial polymers capable of supramolecular assembly

ABSTRACT

Techniques regarding chemical compounds with antimicrobial functionality are provided. For example, one or more embodiments describe herein can comprise a monomer that can comprise a molecular backbone. The molecular backbone can comprise a bis(urea)guanidinium structure covalently bonded to a functional group, which can comprise a radical. Also, the monomer can have supramolecular assembly functionality.

BACKGROUND

The subject disclosure relates to one or more ionenes and/or polyioneneswith antimicrobial functionalities, and more specifically, to one ormore ionene and/or polyionene compositions capable of supramolecularassembly.

SUMMARY

The following presents a summary to provide a basic understanding of oneor more embodiments of the invention. This summary is not intended toidentify key or critical elements, or delineate any scope of theparticular embodiments or any scope of the claims. Its sole purpose isto present concepts in a simplified form as a prelude to the moredetailed description that is presented later. In one or more embodimentsdescribed herein, methods and/or compositions regarding ionenes and/orpolyionenes with antimicrobial functionality are described.

According to an embodiment, a monomer is provided. The monomer cancomprise a molecular backbone comprising a bis(urea)guanidiniumstructure covalently bonded to a functional group, which can comprise aradical. The monomer can have supramolecular assembly functionality.

According to an embodiment, a chemical compound is provided. Thechemical compound can comprise an ionene unit comprising a cationdistributed along a degradable backbone. The degradable backbone cancomprise a bis(urea)guanidinium structure. Also, the ionene unit hasantimicrobial functionality.

According to an embodiment, a method is provided. The method cancomprise aminolyzing an ester group of a monomer with an aminolysisreagent. The monomer can comprise the ester group covalently bonded to aguanidinium group. Also, the aminolyzing can form a molecular backbonethat can comprise a bis(urea)guanidinium structure.

According to an embodiment, a method is provided. The method cancomprise dissolving an amine monomer with an electrophile in a solvent.The amine monomer can comprise a molecular backbone. The molecularbackbone can comprise a bis(urea)guanidinium structure. The method canalso comprise polymerizing the amine monomer and the electrophile toform an ionene unit. Further, the ionene unit can comprise a cationlocated along the molecular backbone. Also, the ionene unit can haveantimicrobial functionality.

According to an embodiment, a method is provided. The method cancomprise dissolving a first amine monomer, a second amine monomer, andan electrophile in solvent. The first amine monomer can comprise amolecular backbone, which can comprise a bis(urea)guanidinium structure.The second amine monomer can comprise a degradable backbone, which cancomprise a terephthalamide structure. The method can further comprisepolymerizing the first amine monomer and the second amine monomer withthe electrophile to form a copolymer. The copolymer can comprise a firstcation distributed along the molecular backbone and a second cationdistributed along the degradable backbone. Also, the copolymer can haveantimicrobial functionality.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1A illustrates a diagram of an example, non-limiting ionene unit inaccordance with one or more embodiments described herein.

FIG. 1B illustrates a diagram of an example, non-limiting lysis processthat can be performed by one or more ionene units in accordance with oneor more embodiments described herein.

FIG. 2 illustrates a diagram of an example, non-limiting chemicalformula that can characterize one or more amine monomers in accordancewith one or more embodiments described herein.

FIG. 3 illustrates a flow diagram of an example, non-limiting methodthat can facilitate generating one or more amine monomers in accordancewith one or more embodiments described herein.

FIG. 4A illustrates a diagram of an example, non-limiting scheme thatcan facilitate generating one or more amine monomers in accordance withone or more embodiments described herein.

FIG. 4B illustrates another diagram of an example, non-limiting schemethat can facilitate generating one or more amine monomers in accordancewith one or more embodiments described herein.

FIG. 5 illustrates a diagram of an example, non-limiting chemicalformula that can characterized one or more ionene units in accordancewith one or more embodiments described herein.

FIG. 6 illustrates a flow diagram of an example, non-limiting methodthat can facilitate generating one or more ionene units in accordancewith one or more embodiments described herein.

FIG. 7A illustrates a diagram of an example, non-limiting scheme thatcan facilitate generating one or more ionene units in accordance withone or more embodiments described herein.

FIG. 7B illustrates another diagram of an example, non-limiting schemethat can facilitate generating one or more ionene units in accordancewith one or more embodiments described herein.

FIG. 8 illustrates a diagram of an example, non-limiting chemicalformula that can characterized one or more ionene units in accordancewith one or more embodiments described herein.

FIG. 9 illustrates a flow diagram of an example, non-limiting methodthat can facilitate generating one or more ionene units in accordancewith one or more embodiments described herein.

FIG. 10A illustrates a diagram of an example, non-limiting scheme thatcan facilitate generating one or more ionene units in accordance withone or more embodiments described herein.

FIG. 10B illustrates another diagram of an example, non-limiting schemethat can facilitate generating one or more ionene units in accordancewith one or more embodiments described herein.

FIG. 11 illustrates a diagram of an example, non-limiting chemicalformula that can characterized one or more ionene units in accordancewith one or more embodiments described herein.

FIG. 12 illustrates a flow diagram of an example, non-limiting methodthat can facilitate generating one or more ionene units in accordancewith one or more embodiments described herein.

FIG. 13 illustrates a diagram of an example, non-limiting scheme thatcan facilitate generating one or more ionene units in accordance withone or more embodiments described herein.

FIG. 14 illustrates a diagram of an example, non-limiting chart that candepict antimicrobial functionality of various ionene compositions inaccordance with one or more of the embodiments described herein.

FIG. 15 illustrates a diagram of an example, non-limiting graph that candepict hemolysis activity of various ionene compositions in accordancewith one or more of the embodiments described herein.

FIG. 16A illustrates a diagram of an example, non-limiting graph thatcan depict cell viability of an ionene composition in accordance withone or more embodiments described herein.

FIG. 16B illustrates a diagram of an example, non-limiting graph thatcan depict hemolysis activity of various ionene compositions inaccordance with one or more of the embodiments described herein.

FIG. 17 illustrates a diagram of an example, non-limiting method thatcan facilitate killing of a pathogen with an ionene in accordance withone or more embodiments described herein.

DETAILED DESCRIPTION

The following detailed description is merely illustrative and is notintended to limit embodiments and/or application or uses of embodiments.Furthermore, there is no intention to be bound by any expressed orimplied information presented in the preceding Background or Summarysections, or in the Detailed Description section.

One or more embodiments are now described with reference to thedrawings, wherein like referenced numerals are used to refer to likeelements throughout. In the following description, for purposes ofexplanation, numerous specific details are set forth in order to providea more thorough understanding of the one or more embodiments. It isevident, however, in various cases, that the one or more embodiments canbe practiced without these specific details.

The discovery and refinement of antibiotics was one of the crowningachievements in the 20^(th) century that revolutionized healthcaretreatment. For example, antibiotics such as penicillin, ciprofloxacinand, doxycycline can achieve microbial selectivity through targeting anddisruption of a specific prokaryotic metabolism, while concurrently,remaining benign toward eukaryotic cells to afford high selectivity. Ifproperly dosed, they could eradicate infection. Unfortunately, thistherapeutic specificity of antibiotics also leads to their undoing asunder-dosing (incomplete kill) allows for minor mutative changes thatmitigate the effect of the antibiotic leading to resistance development.Consequently, nosocomial infections, caused by medication-resistantmicrobes such as methicillin-resistant Staphylococcus aureus (MRSA),multi-medication-resistant Pseudomonas aeruginosa andvancomycin-resistant Enterococci (VRE) have become more prevalent. Anadded complexity is the pervasive use of antimicrobial agents inself-care products, sanitizers and hospital cleaners etc, includinganilide, bis-phenols, biguanides and quaternary ammonium compounds,where a major concern is the development of cross- and co-resistancewith clinically used antibiotics, especially in a hospital setting.Another unfortunate feature with triclosan, for example, is itscumulative and persistent effects in the skin. Moreover, biofilms havebeen associated with numerous nosocomial infections and implant failure,yet the eradication of biofilms is an unmet challenge to this date.Since antibiotics are not able to penetrate through extracellularpolymeric substance that encapsulates bacteria in the biofilm, furthercomplexities exist that lead to the development of medicationresistance.

However, polymers having a cationic charge can provide electrostaticdisruption of the bacterial membrane interaction. Furthermore, cationicpolymers are readily made amphiphilic with addition of hydrophobicregions permitting both membrane association and integration/lysis. Theamphiphilic balance has shown to play an important effect not only inthe antimicrobial properties but also in the hemolytic activity. Many ofthese antimicrobial polymers show relatively low selectivity as definedby the relative toxicity to mammalian cells or hemolysis relative topathogens.

Additionally, chemical compound (e.g., monomers and/or polymers) thatcan supramolecularly assemble with biological entities can demonstrate ahigh efficacy regarding the eradication of infections. In particular,chemical compounds with numerous hydrogen bond donors and/or acceptorsare capable of assembling on the surface of a microbe.

Therefore, various embodiments described herein can regard chemicalcompounds (e.g., monomers and/or polymers) that can comprise one or moreionenes with antimicrobial functionality. Additionally, one or more ofthe ionenes described herein can have antimicrobial functionality and/orsupramolecular assembly functionality. For example, one or more of theionenes described herein can comprise one or more bis(urea) guanidiniumstructures.

As used herein, the term “ionene” can refer to a polymer unit, acopolymer unit, and/or a monomer unit that can comprise a nitrogencation and/or a phosphorus cation distributed along, and/or locatedwithin, a molecular backbone, thereby providing a positive charge.Example nitrogen cations include, but are not limited to: quaternaryammonium cations, protonated secondary amine cations, protonatedtertiary amine cations, and/or imidazolium cations. Example, phosphoruscations include, but are not limited to: quaternary phosphonium cations,protonated secondary phosphine cations, and protonated tertiaryphosphine cations. As used herein, the term “molecular backbone” canrefer to a central chain of covalently bonded atoms that form theprimary structure of a molecule. In various embodiments describedherein, side chains can be formed by bonding one or more functionalgroups to a molecular backbone. As used herein, the term “polyionene”can refer to a polymer that can comprise a plurality of ionenes. Forexample, a polyionene can comprise a repeating ionene.

FIG. 1A illustrates a diagram of an example, non-limiting ionene unit100 in accordance with one or more embodiments described herein. Theionene unit 100 can comprise a molecular backbone 102, one or morecations 104, and/or one or more hydrophobic functional groups 106. Invarious embodiments, an ionene and/or a polyionene described herein cancomprise the ionene unit 100. For example, a polyionene described hereincan comprise a plurality of ionenes bonded together, wherein the bondedionenes can have a composition exemplified by ionene unit 100.

The molecular backbone 102 can comprise a plurality of covalently bondedatoms (illustrated as circles in FIGS. 1A and 1B). The atoms can bebonded in any desirable formation, including, but not limited to: chainformations, ring formations, and/or a combination thereof. The molecularbackbone 102 can comprise one or more chemical structures including, butnot limited to: alkyl structures, aryl structures, alkane structures,aldehyde structures, ester structures, carboxyl structures, carbonylstructures, amine structures, amide structures, phosphide structures,phosphine structures, a combination thereof, and/or the like. One ofordinary skill in the art will recognize that the number of atoms thatcan comprise the molecular backbone can vary depending of the desiredfunction of the ionene unit 100. For example, while nineteen atoms areillustrated in FIG. 1A, a molecular backbone 102 that can comprisedozens, hundreds, and/or thousands of atoms is also envisaged.

Located within the molecular backbone 102 are one or more cations 104.As described above, the one or more cations 104 can comprise nitrogencations and/or phosphorous cations. The cations 104 can be distributedalong the molecular backbone 102, covalently bonded to other atomswithin the molecular backbone 102. In various embodiments, the one ormore cations 104 can comprise at least a portion of the molecularbackbone 102. One of ordinary skill in the art will recognize that thenumber of a cations 104 that can comprise the ionene unit 100 can varydepending of the desired function of the ionene unit 100. For example,while two cations 104 are illustrated in FIG. 1A, an ionene unit 100that can comprise dozens, hundreds, and/or thousands of cations 104 isalso envisaged. Further, while FIG. 1A illustrates a plurality ofcations 104 evenly spaced apart, other configurations wherein thecations 104 are not evenly spaced apart are also envisaged. Also, theone or more cations 104 can be located at respective ends of themolecular backbone 102 and/or at intermediate portions of the molecularbackbone 102, between two or more ends of the molecular backbone 102.The one or more cations 104 can provide a positive charge to one or morelocations of the ionene unit 100.

The one or more hydrophobic functional groups 106 can be bonded to themolecular backbone 102 to form a side chain. The one or more of thehydrophobic functional groups 106 can be attached to the molecularbackbone 102 via bonding with a cation 104. Additionally, one or morehydrophobic functional groups 106 can be bonded to an electricallyneutral atom of the molecular backbone 102. The ionene unit 100 cancomprise one or more hydrophobic functional groups 106 bonded to: one ormore ends of the molecular backbone 102, all ends of the molecularbackbone 102, an intermediate portion (e.g., a portion between two ends)of the molecular backbone 102, and/or a combination thereof.

While a biphenyl group is illustrated in FIG. 1A as the hydrophobicfunctional group 106, other functional groups that are hydrophobic arealso envisaged. Example, hydrophobic functional groups 106 can include,but are not limited to: alkyl structures, aryl structures, alkanestructures, aldehyde structures, ester structures, carboxyl structures,carbonyl structures, carbonate structures, alcohol structures, acombination thereof, and/or the like. In various embodiments, the one ormore hydrophobic functional groups 106 can comprise the same structure.In other embodiments, one or more of the hydrophobic functional groups106 can comprise a first structure and one or more other hydrophobicfunctional groups 106 can comprise another structure.

FIG. 1B illustrates a diagram of an example, non-limiting lysis process108 that can be facilitated by the ionene unit 100 in accordance withone or more embodiments described herein. Repetitive description of likeelements employed in other embodiments described herein is omitted forsake of brevity. The lysis process 108 can comprise a plurality ofstages, which can collectively comprise an attack mechanism that can beperformed by the ionene unit 100 against a pathogen cell. Examplepathogen cells can include, but are not limited to: Gram-positivebacteria cells, Gram-negative bacteria cells, fungi cells, and/or yeastcells.

The target pathogen cell can comprise a membrane having a phospholipidbilayer 110. In various embodiments, the membrane can be anextracellular matrix. The phospholipid bilayer 110 can comprise aplurality of membrane molecules 112 covalently bonded together, and themembrane molecules 112 can comprise a hydrophilic head 114 and one ormore hydrophobic tails 116. Further, one or more of the plurality ofmembrane molecules 112 can be negatively charged (as illustrated in FIG.1B with a “−” symbol).

At 118, electrostatic interaction can occur between the positivelycharged cations 104 of the ionene unit 100 and one or more negativelycharged membrane molecules 112. For example, the negative charge of oneor more membrane molecules 112 can attract the ionene unit 100 towardsthe membrane (e.g., the phospholipid bilayer 110). Also, theelectrostatic interaction can electrostatically disrupt the integrity ofthe membrane (e.g., phospholipid bilayer 110). Once the ionene unit 100has been attracted to the membrane (e.g., phospholipid bilayer 110),hydrophobic membrane integration can occur at 120. For example, at 120one or more hydrophobic functional groups 106 of the ionene unit 100 canbegin to integrate themselves into the phospholipid bilayer 110. Whilethe positively charged portions of the ionene unit 100 are attracted,and electrostatically disrupting, one or more negatively chargedmembrane molecules 112 (e.g., one or more hydrophilic heads 114), theone or more hydrophobic functional groups 106 can insert themselvesbetween the hydrophilic heads 114 to enter a hydrophobic region createdby the plurality of hydrophobic tails 116.

As a result of the mechanisms occurring at 118 and/or 120,destabilization of the membrane (e.g., the phospholipid bilayer 110) canoccur at 122. For example, the one or more hydrophobic functional groups106 can serve to cleave one or more negatively charged membranemolecules 112 from adjacent membrane molecules 112, and the positivelycharged ionene unit 100 can move the cleaved membrane segment (e.g.,that can comprise one or more negatively charged membrane molecules 112and/or one or more neutral membrane molecules 112 constituting a layerof the phospholipid bilayer 110) away from adjacent segments of themembrane (e.g., adjacent segments of the phospholipid bilayer 110). Ascleaved segments of the membrane (e.g., the phospholipid bilayer 110)are pulled away, they can fully detach from other membrane molecules 112at 124, thereby forming gaps in the membrane (e.g., the phospholipidbilayer 110). The formed gaps can contribute to lysis of the subjectpathogen cell. In various embodiments, a plurality of ionene units 100can perform the lysis process 108 on a cell simultaneously. Furthermore,the ionene units 100 participating in a lysis process 108 need notperform the same stages of the attack mechanism at the same time.

FIG. 2 illustrates a diagram of an example, non-limiting chemicalformula 200 that can characterize the structure of an amine monomer thatcan be polymerized to form a variety of ionene units 100 in accordancewith one or more embodiments described herein. Repetitive description oflike elements employed in other embodiments described herein is omittedfor sake of brevity.

As shown in FIG. 2, one or more amine monomer characterized by chemicalformula 200 can comprise a degradable molecular backbone 102. Further,the molecular backbone 102 can comprise one or more bis(urea)guanidiniumstructures. In various embodiments, the one or more amine monomerscharacterized by chemical formula 200 can be derived from1,3-bis(butoxycarbonyl)guanidine, wherein the one or more guanidiniumgroups of the one or more bis(urea)guanidinium structures can be derivedfrom the 1,3-bis(butoxycarbonyl)guanidine. However, one or moreembodiments of chemical formula 200 can comprise one or morebis(urea)guanidium structures derived from one or more molecules otherthan 1,3-bis(butoxycarbonyl)guanidine.

The one or more amine monomers characterized by chemical formula 200 canalso comprise one or more functional groups covalently boned to the oneor more bis(urea)guanidium structures. For example, as shown in FIG. 2,“R₁” can represent a first functional group 202 covalently bonded to theone or more bis(urea)guanidium structures. One or more first functionalgroup 202 can comprise one or more amino groups, one or more phosphinegroups, and/or one or more ester groups. For example, the firstfunctional group 202 can comprise one or more primary amino groups, oneor more secondary amino groups, one or more tertiary amino groups, oneor more imidazole groups, and/or one or more heterocycles (e.g., one ormore pyridine groups). In another example, the first functional group202 can comprise one or more primary phosphines, one or more secondaryphosphines, and/or one or more tertiary phosphines. In another example,the first functional group 202 can comprise one or more ester groups,which can comprise one or more alkyl groups and/or one or more arylgroups. Thus, the first functional group 202 can comprise: one or moregroups (e.g., amino groups and/or phosphine groups) that cansubsequently become cationic groups (e.g., comprising one or morecations 104) during a polymerization of the one or more amine monomerscharacterized by chemical formula 200; and/or one or more groups (e.g.,ester groups) that can contribute degradability to the molecularbackbone 102 of the one or more amine monomers characterized by chemicalformula 200.

As shown in FIG. 2, “R₂” can represent a second functional group 204covalently bonded to the one or more bis(urea)guanidium structures. Oneor more second functional groups 204 can comprise one or more radicals,which can subsequently form one or more cations 104 in a polymerizationof the one or more amine monomers characterized by chemical formula 200.The second functional group 204 can comprise one or more amino groupsand/or one or more phosphine groups. For example, the second functionalgroup 204 can comprise one or more primary amino groups, one or moresecondary amino groups, one or more tertiary amino groups one or moreimidazole groups, and/or one or more heterocycles (e.g., one or morepyridine groups). In another example, the second functional group 204can comprise one or more primary phosphines, one or more secondaryphosphines, and/or one or more tertiary phosphines. In one or moreembodiments, the first functional group 202 and/or the second functionalgroup 204 can comprise different structures. In various embodiments, thefirst functional group 202 and/or the second functional group 204 cancomprise the same structure.

FIG. 3 illustrates a flow diagram of an example, non-limiting method 300that can facilitate generating one or more amine monomers that can becharacterized by chemical formula 200. Repetitive description of likeelements employed in other embodiments described herein is omitted forsake of brevity.

At 302, the method 300 can comprise dissolving one or more monomers withone or more aminolysis reagents in a solvent. The one or more monomerscan comprise a molecular backbone 102, which can comprise one or moreester groups covalently bonded to one or more guanidinium groups.Additionally, the one or more monomers can further comprise a structureselected from a group that can include, but is not limited to: alkylamine groups, hetero cyclic amine groups, a combination thereof, and/orthe like. Moreover, the one or more monomers can be degradable (e.g.,biodegradable). In one or more embodiments, the one or more monomers cancomprise 1,3-bis(butoxycarbonyl)guanidine.

The one or more aminolysis reagents can comprise one or more moleculesthat can facilitate an aminolysis process. For example, the one or moreaminolysis reagents can be diamines. A first amino group of the diaminescan include, but is not limited to, a primary amino group and/or asecondary amino group. Also, a second amino group of the diamines caninclude, but is not limited to: a primary amino group, a secondary aminogroup, a tertiary amino group, and/or an imidazole group. For example,in one or more embodiments the secondary amino group can be a tertiaryamino group and/or an imidazole group.

The solvent can be an organic solvent. Additionally, the solvent can bean aprotic solvent, a dipolar solvent, and/or an alcohol. Examplesolvents can include but are not limited to: dimethyl formamide (“DMF”),methanol, tetrahydrofuran (“THF), a combination thereof, and/or thelike. To facilitate the dissolving, the method 300 can further comprisestirring one or more amine monomers, the one or more aminolysisreagents, and the solvent at a temperature greater than or equal to 15degrees Celsius (° C.) and less than or equal to 150° C. for a period oftime greater than or equal to 8 hours and less than or equal to 72 hours(e.g., greater than or equal to 12 hours and less than or equal to 24hours). Additionally, an organocatylst (e.g., triazabicyclodecene(“TBD”)) can be dissolved at 302.

At 304, the method 300 can comprise aminolyzing one or more ester groupsof the one or more monomers with the aminolysis reagent (e.g., adiamine) to form one or more amine monomers that can be characterized bychemical formula 200. For example, the one or more first amino groups ofone or more diamine aminolysis reagents can donate a hydrogen tofacilitate covalent bonding of the aminolysis agent with one or moreester groups of the one or more amino monomers. As a result of bondingthe one or more first amino groups of one or more diamine aminolysisreagents to one or more ester groups of the one or more monomers, one ormore second amino groups of the one or more diamines can form the firstfunctional group 202 and/or the second functional group 204 (e.g.,generation of one or more urea linkages).

For example, an amine monomer formed at 304 (e.g., characterized bychemical formula 200) can comprise a molecular backbone 102 with one ormore bis(urea)guanidinium structures. For example, the one or more ureagroups of the one or more bis(urea) guanidinium structures can be formedat 304 by replacing an oxygen of one or more ester groups of the monomerreactant with a nitrogen of one or more first amino groups of theaminolysis reagent. Further, one or more functional groups (e.g., firstfunctional group 202 and/or second functional group 204) can be bondedto the one or more bis(urea)guanidinium structures and can comprise oneor more second amino groups of the aminolysis reagent. For instance, oneor more second amino groups of the aminolysis reagent can comprise oneor more tertiary amino groups and/or one or more imidazole groups; thus,said one or more second amino groups can comprise one or more functionalgroups (e.g., first functional group 202 and/or second functional group204) covalently bonded to one or more bis(urea)guanidinium structures at304.

FIG. 4A can illustrate an example, non-limiting scheme 400 that candepict the generation of one or more amine monomers (e.g., first aminemonomer 402, which can be characterized by chemical formula 200) inaccordance with one or more embodiments described herein (e.g., method300). Repetitive description of like elements employed in otherembodiments described herein is omitted for sake of brevity. Thus,scheme 400 can depict a generation of one or more amine monomers (e.g.,first amine monomer 402, which can be characterized by chemical formula200) in accordance with the various features of method 300. While one ormore particular amine reactants (e.g., amine monomer reactant 404),aminolysis reagents, solvents, and/or catalysts are depicted; additionalembodiments of scheme 400 are also envisaged. For example, the principalmechanisms of scheme 400 can be applied to any amine reactant (e.g.,comprising a plurality ester groups bonded to one or more guanidiumgroups), aminolysis reagents, solvents, and/or catalysts in accordancewith the various features described herein (e.g., with reference tochemical formula 200 and/or method 300).

As shown in FIG. 4A, scheme 400 can depict an aminolysis (e.g., inaccordance with method 300) of one or more amine monomer reactants 404(e.g., 1,3-bis(butoxycarbonyl)guanidine) with one or more aminolysisreagents (e.g., 3-(dimethylamino)-1-propylamine) to generate one or moreamine monomers (e.g., first amine monomer 402, which can becharacterized by chemical formula 200). For example, the one or moreamine monomer reactants 404 (e.g., 1,3-bis(butoxycarbonyl)guanidine) canbe dissolved with the one or more aminolysis reagent (e.g.,3-(dimethylamino)-1-propylamine) in a solvent (e.g., THF) in thepresence of a catalyst (e.g., TBD). The one or more amine monomerreactants 404 (e.g., 1,3-bis(butoxycarbonyl)guanidine), the one or moreaminolysis reagents (e.g., 3-(dimethylamino)-1-propylamine), the solvent(e.g., THF), and/or the catalyst (e.g., TBD) can be stirred at atemperature greater than or equal to 15° C. and less than or equal to150° C. (e.g., 68° C.) for a period of time greater than or equal to 8hours and less than or equal to 72 hours (e.g., greater than or equal to12 hours and less than or equal to 24 hours).

The one or more amine monomers (e.g., first amine monomer 402, which canbe characterized by chemical formula 200) can comprise a molecularbackbone 102 having one or more bis(urea)guanidinium structures bondedto a first functional group 202 and/or a second functional group 204. Anaminolysis (e.g., the aminolysis at 304) can replace one or more oxygensof the one or more ester groups of the one or more amine monomerreactants 404 with one or more first amino groups of the one or moreaminolysis reagents (3-(dimethylamino)-1-propylamine) to form one ormore urea structures, wherein the one or more second amino groups of theone or more aminolysis reagents can thereby comprise the one or morefirst functional groups 202 and/or second functional groups 204. The oneor more first functional groups 202 and/or the one or more secondfunctional groups 204 of the one or more amine monomers (e.g., firstamine monomers 402) can have the same structure. For example, the one ormore first functional groups 202 and/or the one or more secondfunctional groups 204 can both comprise a tertiary amino groupcomprising the second amino group of the aminolysis reagent (e.g.,3-(dimethylamino)-1-propylamine).

FIG. 4B can illustrate an example, non-limiting scheme 406 that candepict the generation of one or more amine monomers (e.g., second aminemonomers 408, which can be characterized by chemical formula 200) inaccordance with one or more embodiments described herein (e.g., method300). Repetitive description of like elements employed in otherembodiments described herein is omitted for sake of brevity. Thus,scheme 400 can depict a generation of one or more amine monomers (e.g.,second amine monomers 408, which can be characterized by chemicalformula 200) in accordance with the various features of method 300.While one or more particular amine reactants (e.g., amine monomerreactant 404), aminolysis reagents, and/or solvents are depicted;additional embodiments of scheme 406 are also envisaged. For example,the principal mechanisms of scheme 406 can be applied to any aminereactants (e.g., comprising a plurality ester groups bonded to one ormore guanidium groups), aminolysis reagents, and/or solvents, inaccordance with the various features described herein (e.g., withreference to chemical formula 200 and/or method 300).

As shown in FIG. 4B, scheme 406 can depict an aminolysis (e.g., inaccordance with method 300) of one or more amine monomer reactants 404(e.g., 1,3-bis(butoxycarbonyl)guanidine) with one or more aminolysisreagents (e.g., (3-aminopropyl)imidazole) to generate one or more aminemonomers (e.g., second amine monomer 408, which can be characterized bychemical formula 200). For example, the one or more amine monomerreactants 404 (e.g., 1,3-bis(butoxycarbonyl)guanidine) can be dissolvedwith the one or more aminolysis reagent (e.g., (3-aminopropyl)imidazole)in a solvent (e.g., THF). The aminolysis of scheme 406 can be aself-catalyzed process. The one or more amine monomer reactants 404(e.g., 1,3-bis(butoxycarbonyl)guanidine), the one or more aminolysisreagents (e.g., (3-aminopropyl)imidazole), and/or the solvent (e.g.,THF) can be stirred at a temperature greater than or equal to 15° C. andless than or equal to 150° C. (e.g., 68° C.) for a period of timegreater than or equal to 8 hours and less than or equal to 72 hours(e.g., greater than or equal to 12 hours and less than or equal to 24hours).

The one or more amine monomers (e.g., second amine monomer 408, whichcan be characterized by chemical formula 200) can comprise a molecularbackbone 102 having one or more bis(urea)guanidinium structures bondedto a first functional group 202 and/or a second functional group 204. Anaminolysis (e.g., the aminolysis at 304) can replace one or more oxygensof the one or more ester groups of the one or more amine monomerreactants 404 with one or more first amino groups of the one or moreaminolysis reagents ((3-aminopropyl)imidazole) to form one or more ureastructures, wherein the one or more second amino groups of the one ormore aminolysis reagents can thereby comprise the one or more firstfunctional groups 202 and/or second functional groups 204. The one ormore first functional groups 202 and/or the one or more secondfunctional groups 204 of the one or more amine monomers (e.g., secondamine monomers 408) can have the same structure. For example, the one ormore first functional groups 202 and/or the one or more secondfunctional groups 204 can both comprise an imidazole group comprisingthe second amino group of the aminolysis reagent (e.g.,(3-aminopropyl)imidazole).

FIG. 5 illustrates a diagram of an example, non-limiting chemicalformula 500 that can characterize the structure of an ionene unit 100 inaccordance with one or more embodiments described herein. Repetitivedescription of like elements employed in other embodiments describedherein is omitted for sake of brevity. In one or more embodiments, theionene unit 100 characterized by chemical formula 500 can form amonomer. In various embodiments, a plurality of ionene units 100characterized by chemical formula 500 can be covalently bond together toform a polymer (e.g., an alternating copolymer and/or a randomcopolymer).

As shown in FIG. 5, an ionene unit 100 characterized by chemical formula500 can comprise a degradable molecular backbone 102. Further, thedegradable molecular backbone 102 can comprise one or morebis(urea)guanidinium structures. In various embodiments, the ionene unit100 characterized by chemical formula 500 can be derived from1,3-bis(butoxycarbonyl)guanidine, wherein the one or more guanidiniumgroups can be derived from the 1,3-bis(butoxycarbonyl)guanidine.However, one or more embodiments of chemical formula 500 can compriseone or more bis(urea)guanidinium structures derived from one or moremolecules other than 1,3-bis(butoxycarbonyl)guanidine.

The “X” in FIG. 5 can represent the one or more cations 104. Forexample, “X” can represent one or more cations 104 selected from a groupthat can include, but is not limited to: one or more nitrogen cations,one or more phosphorus cations, and/or a combination thereof. Forinstance, “X” can represent one or more nitrogen cations selected from agroup that can include, but is not limited to: one or more protonatedsecondary amine cations, one or more protonated tertiary amine cations,one or more quaternary ammonium cations, one or more imidazoliumcations, and/or a combination thereof. In another instance, “X” canrepresent one or more phosphorus cations selected from a group that caninclude, but is not limited to: one or more protonated secondaryphosphine cations, one or more protonated tertiary phosphine cations,one or more quaternary phosphonium cations, and/or a combinationthereof.

The one or more cations 104 (e.g., represented by “X” in chemicalformula 500) can be covalently bonded to one or more linkage groups toform, at least a portion, of the degradable molecular backbone 102. Theone or more linkage groups can link the one or more cations 104 to theone or more bis(urea)guanidinium structures, thereby comprising themolecular backbone 102. The “L” in FIG. 5 can represent the one or morelinkage groups. The one or more linkage groups can comprise anystructure in compliance with the various features of the molecularbackbone 102 described herein. For example, the one or more linkagegroups can have any desirable formation, including, but not limited to:chain formations, ring formations, and/or a combination thereof. The oneor more linkage groups can comprise one or more chemical structuresincluding, but not limited to: alkyl structures, aryl structures, alkanestructures, aldehyde structures, ester structures, carboxyl structures,carbonyl structures, a combination thereof, and/or the like. Forinstance, “L” can represent one or more linkage groups that can comprisean alkyl chain having greater than or equal to two carbon atoms and lessthan or equal to 15 carbon atoms.

As shown in FIG. 5, in various embodiments, an ionene unit 100characterized by chemical formula 500 can comprise cations 104 (e.g.,represented by “X”) at a plurality of locations along the molecularbackbone 102. For example, cations 104 can be located at either end ofthe molecular backbone 102 (e.g., as illustrated in FIG. 5). However, inone or more embodiments of chemical formula 500, the molecular backbone102 can comprise less or more cations 104 than the two illustrated inFIG. 5.

Further, the “R” shown in FIG. 5 can represent the one or morehydrophobic functional groups 106 in accordance with the variousembodiments described herein. For example, the one or more hydrophobicfunctional groups 106 can comprise one or more alkyl groups and/or oneor more aryl groups. For instance, the hydrophobic functional group 106can be derived from one or more dialkyl halides. The one or morehydrophobic functional groups 106 (e.g., represented by “R” in FIG. 5)can be covalently bonded to one or more of the cations 104 (e.g.,represented by “X” in FIG. 5) and/or the molecular backbone 102, whichcan comprise the one or more cations 104 (e.g., represented by “X” inFIG. 5), one or more linkage groups (e.g., represented by “L” in FIG.5), and/or one or more bis(urea)guanidinium structures.

Moreover, an ionene and/or polyionene characterized by chemical formula500 can comprise a single ionene unit 100 or a repeating ionene unit100. For example, the “n” shown in FIG. 5 can represent a first integergreater than or equal to one and less than or equal to one thousand.Thus, an ionene unit 100 characterized by chemical formula 500 can formmonomers and/or polymers (e.g., alternating copolymers and/or randomcopolymers).

FIG. 6 illustrates another flow diagram of an example, non-limitingmethod 600 that can generate one or more ionene units 100, which can becharacterized by chemical formula 500, in accordance with one or moreembodiments described herein. Repetitive description of like elementsemployed in other embodiments described herein is omitted for sake ofbrevity.

At 602, the method 600 can comprise dissolving one or more aminemonomers (e.g., characterized by chemical formula 200) with one or moreelectrophiles in a solvent. The one or more amine monomers (e.g.,characterized by chemical formula 200) can comprise a molecular backbone102 that has one or more bis(urea)guanidinium structures. The one ormore amine monomers can be degradable (e.g., biodegradable) and/orcomprise one or more functional groups (e.g., first functional group 202and/or second functional group 204), which can be ionized. The one ormore amine monomers can further comprise a structure selected from agroup that can include, but is not limited to: alkyl amine groups,hetero cyclic amine groups, a combination thereof, and/or the like. Forexample, the one or more amine monomers can be characterized by chemicalformula 200 and/or generated by method 400. For instance, the one ormore amine monomers can comprise first amine monomer 402 depicted inFIG. 4A and/or second amine monomer 408 depicted in FIG. 4B. In one ormore embodiments, the one or more amine monomers (e.g., characterized bychemical formula 200) can be prepared using one or more techniques otherthan those described in regards to method 300.

The one or more electrophiles can comprise, for example, one or morealkyl halides (e.g., dialkyl halides). For instance, the one or moreelectrophiles can comprise one or more dialkyl halides having chlorideand/or bromide. Example electrophiles can include, but are not are notlimited to: p-xylylene dichloride, 4,4′-bis(chloromethyl)biphenyl;1,4-bis(bromomethyl)benzene; 4,4′-bis(bromomethyl)biphenyl;1,4-bis(iodomethyl)benzene; 1,6-dibromohexane; 1,8-dibromooctane;1,12-dibromododecane; 1,6-dichlorohexane; 1,8-dichlorooctane; acombination thereof; and/or the like.

The solvent can be an organic solvent. Additionally, the solvent can bean aprotic solvent, a dipolar solvent, and/or an alcohol. Examplesolvents can include but are not limited to: DMF, methanol, acombination thereof, and/or the like. For example, DMF can be used asthe solvent as it can dissolve the reactants at elevated temperatures.In one or more embodiments, equimolar amounts of the plurality ofdegradable amine monomers and the one or more electrophiles can bedissolved in the solvent.

To facilitate the dissolving at 602, the method 600 can optionallycomprise stirring the one or more amine monomers, the one or moreelectrophiles, and the solvent at a temperature greater than or equal to15° C. and less than or equal to 150° C. for a period of time greaterthan or equal to 8 hours and less than or equal to 72 hours (e.g.,greater than or equal to 12 hours and less than or equal to 24 hours).Additionally, an organocatalyst can optionally be added at 602. Example,organocatalysts include, but are not limited to:1,8-diazabicyclo[5.4.0]undec-7-ene (“DBU”),1-(3,5-bis(trifluoromethyl)-phenyl)-3-cyclohexyl-2-thiourea (“TU”), acombination thereof, and/or the like.

At 604, the method 600 can comprise polymerizing the one or more aminemonomers and the one or more electrophiles to form an ionene unit 100.The ionene unit 100 (e.g., characterized by chemical formula 500) cancomprise a cation 104 distributed along a degradable molecular backbone102. The molecular backbone 102 can comprise one or morebis(urea)guanidinium structures (e.g., as illustrated in chemicalformula 500). Further, the ionene unit 100 formed at 604 can haveantimicrobial functionality and/or supramolecular assemblyfunctionality. In one or more embodiments, the polymerizing at 604 canbe performed under nitrogen gas. Additionally, the polymerizing at 604can generate the cation through alkylation and/or quaternation with theone or more electrophiles.

During the polymerization at 604, a nitrogen atom and/or a phosphorusatom located in the one or more amine monomers (e.g., comprising thefirst functional group 202 and/or the second functional group 204) canbe subject to alkylation and/or quaternization; thus, the polymerizationat 604 can conduct a polymer-forming reaction (e.g., formation of theionene unit 100) and an installation of charge (e.g., forming a cation104, including a nitrogen cation and/or a phosphorus cation)simultaneously without a need of a catalyst. Further, one or morehydrophobic functional groups 106 can be derived from the one or moreelectrophiles and/or can be bonded to the one or more cations 104 as aresult of the alkylation and/or quaternization process.

For example, the ionene formed at 604 can comprise one or moreembodiments of the ionene unit 100 and can be characterized by one ormore embodiments of chemical formula 500. For instance, the ionene unit100 formed at 604 can comprise a degradable molecular backbone 102 thatcan comprise one or more cations 104 (e.g., represented by “X” inchemical formula 500), one or more linkage groups (e.g., represented by“L” in chemical formula 500), one or more bis(urea)guanidiniumstructures (e.g., as shown in FIG. 5), and/or one or more hydrophobicfunctional groups 106 (e.g., represented by “R” in chemical formula500). The one or more cations 104 can be nitrogen cations (e.g.,protonated secondary amine cations, protonated tertiary amine cations,quaternary ammonium cations, imidazolium cations, and/or a combinationthereof) and/or phosphorus cations (e.g., quaternary phosphoniumcations). The cations 104 can be linked to the one or morebis(urea)guanidinium structures via one or more linkage groups (e.g.,alkyl groups and/or aryl groups). Further, one or more of the cations104 can be bonded to one or more of the hydrophobic functional groups106. Additionally, the ionene unit 100 formed at 604 can repeat a numberof times greater than or equal to 1 and less than or equal to 1000.

Antimicrobial activity of the repeating ionene units 100 generated bythe methods described herein (e.g., method 600) can be independent ofmolecular weight. Thus, the method 600 can target polymerizationconditions that can extinguish molecular weight attainment by diffusionlimited mechanism (e.g., polymer precipitation) to modest molecularweights (e.g., molecular weights less than 7,000 grams per mole(g/mol)), which can aid in the solubility of the repeating ionene units100 in aqueous media.

FIG. 7A can illustrate an example, non-limiting scheme 700 that candepict the generation of one or more ionene compositions (e.g., firstionene composition 702, which can be characterized by chemical formula500) in accordance with one or more embodiments described herein (e.g.,method 600). Repetitive description of like elements employed in otherembodiments described herein is omitted for sake of brevity. Thus,scheme 700 can depict a generation of one or more ionene compositions(e.g., first ionene composition 702 that can be characterized bychemical formula 500) in accordance with the various features of method600. While one or more particular amine monomers, electrophiles, and/orsolvents are depicted; additional embodiments of scheme 700 are alsoenvisaged. For example, the principal mechanisms of scheme 700 can beapplied to any amine monomer, electrophiles, and/or solvents inaccordance with the various features described herein (e.g., withreference to chemical formula 500 and/or method 600).

As shown in FIG. 7A, scheme 700 can depict a polymerization (e.g., inaccordance with method 600) of one or more amine monomers (e.g., firstamine monomer 402) with one or more electrophiles (e.g., p-xylylenedichloride) to generate one or more ionene compositions (e.g., firstionene composition 702, which can be characterized by chemical formula500). For example, the one or more amine monomers (e.g., first aminemonomer 402) can be dissolved with the one or more electrophiles (e.g.,p-xylylene dichloride) in a solvent (e.g., DMF). The one or more aminemonomers (e.g., first amine monomer 402), the one or more electrophiles(e.g., p-xylylene dichloride), and/or the solvent (e.g., DMF) can bestirred at a temperature greater than or equal to 15° C. and less thanor equal to 150° C. (e.g., 85° C.) for a period of time greater than orequal to 8 hours and less than or equal to 72 hours (e.g., greater thanor equal to 12 hours and less than or equal to 24 hours).

The one or more ionene compositions (e.g., first ionene composition 702,which can be characterized by chemical formula 500) can comprise amolecular backbone 102 having one or more bis(urea)guanidiniumstructures. A polymerization (e.g., the polymerization at 604) cansubject a functional group bonded to the molecular backbone 102 (e.g.,first functional group 202 and/or second functional group 204) to aquaternization with the one or more electrophiles; thereby bonding ahydrophobic group 106 to the molecular backbone 102 and/or forming oneor more cations 104. For example, in scheme 700, the quaternization canform one or more quaternary ammonium cations that can be bonded to boththe molecular backbone 102 (e.g., via a linkage group) and thehydrophobic functional group 106 (e.g., derived from the one or moreelectrophiles). The one or more ionene compositions (e.g., first ionenecomposition 702) can comprise monomers and/or polymers (e.g.,homopolymers, alternating copolymers, and/or random copolymers), whereinthe “n” shown in FIG. 7A can represent an integer greater than or equalto one and less than or equal to one thousand.

FIG. 7B can illustrate an example, non-limiting scheme 704 that candepict the generation of one or more ionene compositions (e.g., firstionene composition 706, which can be characterized by chemical formula500) in accordance with one or more embodiments described herein (e.g.,method 600). Repetitive description of like elements employed in otherembodiments described herein is omitted for sake of brevity. Thus,scheme 704 can depict a generation of one or more ionene compositions(e.g., first ionene composition 702 that can be characterized bychemical formula 500) in accordance with the various features of method600. While one or more particular amine monomers, electrophiles, and/orsolvents are depicted; additional embodiments of scheme 704 are alsoenvisaged. For example, the principal mechanisms of scheme 704 can beapplied to any amine monomer, electrophiles, and/or solvents inaccordance with the various features described herein (e.g., withreference to chemical formula 500 and/or method 600).

As shown in FIG. 7B, scheme 704 can depict a polymerization (e.g., inaccordance with method 600) of one or more amine monomers (e.g., secondamine monomer 408) with one or more electrophiles (e.g., p-xylylenedichloride) to generate one or more ionene compositions (e.g., secondionene composition 706, which can be characterized by chemical formula500). For example, the one or more amine monomers (e.g., second aminemonomer 408) can be dissolved with the one or more electrophiles (e.g.,p-xylylene dichloride) in a solvent (e.g., DMF). The one or more aminemonomers (e.g., second amine monomer 408), the one or more electrophiles(e.g., p-xylylene dichloride), and/or the solvent (e.g., DMF) can bestirred at a temperature greater than or equal to 15° C. and less thanor equal to 150° C. (e.g., 85° C.) for a period of time greater than orequal to 8 hours and less than or equal to 72 hours (e.g., greater thanor equal to 12 hours and less than or equal to 24 hours).

The one or more ionene compositions (e.g., second ionene composition706, which can be characterized by chemical formula 500) can comprise amolecular backbone 102 having one or more bis(urea)guanidiniumstructures. A polymerization (e.g., the polymerization at 604) cansubject a functional group bonded to the molecular backbone 102 (e.g.,first functional group 202 and/or second functional group 204) to analkylation with the one or more electrophiles; thereby bonding ahydrophobic group 106 to the molecular backbone 102 and/or forming oneor more cations 104. For example, in scheme 704, the alkylation can formone or more imidazolium cations that can be bonded to both the molecularbackbone 102 (e.g., via a linkage group) and the hydrophobic functionalgroup 106 (e.g., derived from the one or more electrophiles). The one ormore ionene compositions (e.g., second ionene composition 706) cancomprise monomers and/or polymers (e.g., homopolymers, alternatingcopolymers, and/or random copolymers), wherein the “n” shown in FIG. 7Bcan represent an integer greater than or equal to one and less than orequal to one thousand.

FIG. 8 illustrates a diagram of an example, non-limiting chemicalformula 800 that can characterize the structure of one or morecopolymers in accordance with one or more embodiments described herein.Repetitive description of like elements employed in other embodimentsdescribed herein is omitted for sake of brevity. In one or moreembodiments, the one or more copolymers characterized by chemicalformula 800 can comprise a first ionene unit 100 (e.g., characterized bychemical formula 500) covalently bonded to a second ionene unit 100. Theone or more copolymers characterized by chemical formula 800 can bealternating copolymers and/or random copolymers.

As shown in FIG. 8, a first ionene unit 100 (e.g., characterized bychemical formula 500) can comprise a molecular backbone 102. Further,the molecular backbone 102 can comprise one or more bis(urea)guanidiniumstructures. In various embodiments, the first ionene unit 100 (e.g.,characterized by chemical formula 500) can be derived from1,3-bis(butoxycarbonyl)guanidine, wherein the one or more guanidiniumgroups can be derived from the 1,3-bis(butoxycarbonyl)guanidine.However, one or more embodiments of chemical formula 800 can compriseone or more bis(urea)guanidinium structures derived from one or moremolecules other than 1,3-bis(butoxycarbonyl)guanidine.

The “X₁” in FIG. 8 can represent one or more first cations 104. Forexample, “X₁” can represent one or more first cations 104 selected froma group that can include, but is not limited to: one or more nitrogencations, one or more phosphorus cations, and/or a combination thereof.For instance, “X₁” can represent one or more nitrogen cations selectedfrom a group that can include, but is not limited to: one or moreprotonated secondary amine cations, one or more protonated tertiaryamine cations, one or more quaternary ammonium cations, one or moreimidazolium cations, and/or a combination thereof. In another instance,“X₁” can represent one or more phosphorus cations selected from a groupthat can include, but is not limited to: one or more protonatedsecondary phosphine cations, one or more protonated tertiary phosphinecations, one or more quaternary phosphonium cations, and/or acombination thereof.

The one or more first cations 104 (e.g., represented by “X₁” in chemicalformula 800) can be covalently bonded to one or more first linkagegroups to form, at least a portion, of the molecular backbone 102. Theone or more first linkage groups can link the one or more first cations104 to the one or more bis(urea)guanidinium structures, therebycomprising the molecular backbone 102. The “L₁” in FIG. 8 can representthe one or more first linkage groups. The one or more first linkagegroups can comprise any structure in compliance with the variousfeatures of the molecular backbone 102 described herein. For example,the one or more first linkage groups can have any desirable formation,including, but not limited to: chain formations, ring formations, and/ora combination thereof. The one or more first linkage groups can compriseone or more chemical structures including, but not limited to: alkylstructures, aryl structures, alkane structures, aldehyde structures,ester structures, carboxyl structures, carbonyl structures, acombination thereof, and/or the like. For instance, “L₁” can representone or more first linkage groups that can comprise an alkyl chain havinggreater than or equal to two carbon atoms and less than or equal to 15carbon atoms.

As shown in FIG. 8, in various embodiments, one or more first ioneneunits 100 characterized by chemical formula 800 can comprise firstcations 104 (e.g., represented by “X₁”) at a plurality of locationsalong the molecular backbone 102. For example, first cations 104 can belocated at either end of the molecular backbone 102 (e.g., asillustrated in FIG. 8). However, in one or more embodiments of chemicalformula 800, the molecular backbone 102 can comprise less or more firstcations 104 than the two illustrated in FIG. 8.

Further, the “R” shown in FIG. 8 can represent the one or morehydrophobic functional groups 106 in accordance with the variousembodiments described herein. For example, the one or more hydrophobicfunctional groups 106 can comprise one or more alkyl groups and/or oneor more aryl groups. For instance, the hydrophobic functional group 106can be derived from one or more dialkyl halides. The one or morehydrophobic functional groups 106 (e.g., represented by “R” in FIG. 8)can be covalently bonded to one or more of the first cations 104 (e.g.,represented by “X₁” in FIG. 8) and/or the molecular backbone 102, whichcan comprise the one or more first cations 104 (e.g., represented by“X₁” in FIG. 8), one or more first linkage groups (e.g., represented by“L₁” in FIG. 8), and/or one or more bis(urea)guanidinium structures.

Moreover, one or more copolymers characterized by chemical formula 800can comprise a single first ionene unit 100 or a repeating first ioneneunit 100. For example, the “n” shown in FIG. 8 can represent a firstinteger greater than or equal to one and less than or equal to onethousand.

As shown in FIG. 8, the one or more copolymers that can be characterizedby chemical formula 800 can further comprise a second ionene unit 100,which can comprise a degradable (e.g., biodegradable) molecular backbone102. Further, the degradable molecular backbone 102 can comprise one ormore terephthalamide structures. In various embodiments, the secondionene unit 100 (e.g., characterized by chemical formula 800) can bederived from polyethylene terephthalate (“PET”), wherein the one or moreterephthalamide structures can be derived from the PET. However, one ormore embodiments of chemical formula 800 can comprise one or moreterephthalamide structures derived from one or more molecules other thanPET.

The “X₂” in FIG. 8 can represent one or more second cations 104. Forexample, “X₂” can represent one or more second cations 104 selected froma group that can include, but is not limited to: one or more nitrogencations, one or more phosphorus cations, and/or a combination thereof.For instance, “X₂” can represent one or more nitrogen cations selectedfrom a group that can include, but is not limited to: one or moreprotonated secondary amine cations, one or more protonated tertiaryamine cations, one or more quaternary ammonium cations, one or moreimidazolium cations, and/or a combination thereof. In another instance,“X₂” can represent one or more phosphorus cations selected from a groupthat can include, but is not limited to: one or more protonatedsecondary phosphine cations, one or more protonated tertiary phosphinecations, one or more quaternary phosphonium cations, and/or acombination thereof.

The one or more second cations 104 (e.g., represented by “X₂” inchemical formula 800) can be covalently bonded to one or more secondlinkage groups to form, at least a portion, of the degradable molecularbackbone 102. The one or more second linkage groups can link the one ormore second cations 104 to the one or more terephthalamide structures,thereby comprising the molecular backbone 102. The “L₂” in FIG. 8 canrepresent the one or more second linkage groups. The one or more secondlinkage groups can comprise any structure in compliance with the variousfeatures of the molecular backbone 102 described herein. For example,the one or more second linkage groups can have any desirable formation,including, but not limited to: chain formations, ring formations, and/ora combination thereof. The one or more first linkage groups can compriseone or more chemical structures including, but not limited to: alkylstructures, aryl structures, alkenyl structures, aldehyde structures,ester structures, carboxyl structures, carbonyl structures, acombination thereof, and/or the like. For instance, “L₂” can representone or more second linkage groups that can comprise an alkyl chainhaving greater than or equal to two carbon atoms and less than or equalto 15 carbon atoms.

As shown in FIG. 8, in various embodiments, one or more second ioneneunits 100 characterized by chemical formula 800 can comprise secondcations 104 (e.g., represented by “X₂”) at a plurality of locationsalong the degradable molecular backbone 102. For example, second cations104 can be located at either end of the degradable molecular backbone102 (e.g., as illustrated in FIG. 8). However, in one or moreembodiments of chemical formula 800, the degradable molecular backbone102 can comprise less or more second cations 104 than the twoillustrated in FIG. 8.

Further, one or more hydrophobic functional groups 106 (e.g.,represented by “R” in FIG. 8) can be covalently bonded to one or more ofthe second cations 104 (e.g., represented by “X₂” in FIG. 8) and/or thedegradable molecular backbone 102, which can comprise the one or moresecond cations 104 (e.g., represented by “X₂” in FIG. 8), one or moresecond linkage groups (e.g., represented by “L₂” in FIG. 8), and/or oneor more terephthalamide structures. Additionally, one or morehydrophobic functional groups 106 can be bonded to both one or more ofthe first cations 104 (e.g., represented by “X₁” in FIG. 8) of the oneor more first ionene units 100 and one or more of the second cations 104(e.g., represented by “X₂” in FIG. 8) of the one or more second ioneneunits 100; thereby bonding the one or more first ionene units 100 withthe one or more second ionene units 100.

Moreover, one or more copolymers characterized by chemical formula 800can comprise a single second ionene unit 100 or a repeating secondionene unit 100. For example, the “m” shown in FIG. 8 can represent asecond integer greater than or equal to one and less than or equal toone thousand.

In one or more embodiments, the one or more first cations 104 (e.g.,represented by “X₁”) of the first ionene unit 100 can have the samestructure as the one or more second cations 104 (e.g., represented by“X₂”) of the second ionene unit 100. For example, all the cations 104 ofone or more copolymers characterized by chemical formula 800, includingboth the one or more first cations 104 and/or the one or more secondcations 104, can be quaternary ammonium cations. In another example, allthe cations 104 of one or more copolymers characterized by chemicalformula 800, including both the one or more first cations 104 and/or thesecond one or more cations 104, can be imidazolium cations. In variousembodiments, the one or more first cations 104 (e.g., represented by“X₁”) of the first ionene unit 100 can have different structures thanthe one or more second cations 104 (e.g., represented by “X₂”) of thesecond ionene unit 100. For example, the one or more first cations 104can be quaternary ammonium cations while the one or more second cations104 can be imidazolium cations. In another example, the one or morefirst cations 104 can be imidazolium cations while the one or moresecond cations 104 can be quaternary ammonium cations.

Further, in one or more embodiments, the one or more first linkagegroups (e.g., represented by “L₁”) of the first ionene unit 100 can havethe same structure as the one or more second linkage groups (e.g.,represented by “L₂”) of the second ionene unit 100. In some embodiments,the one or more first linkage groups (e.g., represented by “L₁”) of thefirst ionene unit 100 can have different structures than the one or moresecond linkage groups (e.g., represented by “L₂”) of the second ioneneunit 100.

FIG. 9 illustrates another flow diagram of an example, non-limitingmethod 900 that can generate one or more polyionenes, which can becharacterized by chemical formula 800, in accordance with one or moreembodiments described herein. Repetitive description of like elementsemployed in other embodiments described herein is omitted for sake ofbrevity. Method 900 can facilitate generating one or more copolymers(e.g., characterized by chemical formula 800) comprising a first ioneneunit 100 and/or a second ionene unit 100. The one or more copolymers canbe alternating copolymers and/or random copolymers.

At 902, the method 900 can comprise dissolving one or more first type ofamine monomers (e.g., characterized by chemical formula 200) and one ormore second type of amine monomers with one or more electrophiles in asolvent. The one or more first type of amine monomers (e.g.,characterized by chemical formula 200) can comprise a molecular backbone102 that has one or more bis(urea)guanidinium structures. The one ormore first type of amine monomers can be degradable (e.g.,biodegradable) and/or comprise one or more functional groups (e.g.,first functional group 202 and/or second functional group 204), whichcan be ionized. The one or more first type of amine monomers can furthercomprise a structure selected from a group that can include, but is notlimited to: alkyl amine groups, hetero cyclic amine groups, acombination thereof, and/or the like. For example, the one or more firsttype of amine monomers can be characterized by chemical formula 200and/or generated by method 400. For instance, the one or more first typeof amine monomers can comprise first amine monomer 402 depicted in FIG.4A and/or second amine monomer 408 depicted in FIG. 4B. In one or moreembodiments, the one or more first type of amine monomers (e.g.,characterized by chemical formula 200) can be prepared using one or moretechniques other than those described regarding method 300.

The one or more second type of amine monomers can comprise a degradablemolecular backbone 102 that has one or more terephthalamide structures.The one or more second type of amine monomers can be degradable (e.g.,biodegradable) and/or comprise one or more functional groups, which canbe ionized. The one or more second type of amine monomers can furthercomprise a structure selected from a group that can include, but is notlimited to: alkyl amine groups, hetero cyclic amine groups, acombination thereof, and/or the like. In one or more embodiments, theone or more second type of amine monomers can be tetra-amine monomers.Also, in various embodiments, the one or more second amine monomers canbe derived from an aminolysis of PET.

The one or more electrophiles can comprise, for example, one or morealkyl halides (e.g., dialkyl halides). For instance, the one or moreelectrophiles can comprise one or more dialkyl halides having chlorideand/or bromide. Example electrophiles can include, but are not are notlimited to: p-xylylene dichloride; 4,4′-bis(chloromethyl)biphenyl;1,4-bis(bromomethyl)benzene; 4,4′-bis(bromomethyl)biphenyl;1,4-bis(iodomethyl)benzene; 1,6-dibromohexane; 1,8-dibromooctane;1,12-dibromododecane; 1,6-dichlorohexane; 1,8-dichlorooctane; acombination thereof; and/or the like. The solvent can be an organicsolvent. Additionally, the solvent can be an aprotic solvent, a dipolarsolvent, and/or an alcohol. Example solvents can include but are notlimited to: DMF, methanol, a combination thereof, and/or the like. Forexample, DMF can be used as the solvent as it can dissolve the reactantsat elevated temperatures.

To facilitate the dissolving at 902, the method 900 can optionallycomprise stirring the one or more first type of amine monomers, the oneor more second type of amine monomers, the one or more electrophiles,and the solvent at a temperature greater than or equal to 15° C. andless than or equal to 150° C. for a period of time greater than or equalto 8 hours and less than or equal to 72 hours (e.g., greater than orequal to 12 hours and less than or equal to 24 hours). Additionally, anorganocatlyst can optionally be added at 602. Example, organocatystsinclude, but are not limited to: 1,8-diazabicyclo[5.4.0]undec-7-ene(“DBU”), 1-(3,5-bis(trifluoromethyl)-phenyl)-3-cyclohexyl-2-thiourea(“TU”), a combination thereof, and/or the like.

At 904, the method 900 can comprise polymerizing the one or more firsttype of amine monomers and the one or more second type of amine monomerswith the one or more electrophiles to form a copolymer (e.g., analternating copolymer and/or a random copolymer). The copolymer (e.g.,characterized by chemical formula 800) can comprise one or more firstionene units 100 having one or more first cations 104 distributed alonga molecular backbone 102 derived from the one or more first type ofamine monomers. Said molecular backbone 102 can comprise one or morebis(urea)guanidinium structures (e.g., as illustrated in chemical FIG.8). Further, the copolymer can comprise one or more second ionene units100 having one or more second cations 104 distributed along a degradablemolecular backbone 102 derived from the one or more second type of aminemonomers. Said degradable molecular backbone 102 can comprise one ormore terephthalamide structures (e.g., as illustrated in FIG. 8).Additionally, the copolymer can further comprise one or more hydrophobicfunctional groups 106 that can be bonded to one or more first cations104 of the one or more first ionene units 100 and/or one or more secondcations 104 of the one or more second ionene units 100; thereby bondingthe one or more first ionene units 100 and/or the one or more secondionene units 100 to each other.

Further, the copolymer formed at 904 can have antimicrobialfunctionality and/or supramolecular assembly functionality. In one ormore embodiments, the polymerizing at 904 can be performed undernitrogen gas. Additionally, the polymerizing at 904 can generate the oneor more first cations 104 and/or the one or more second cations 104through alkylation and/or quaternation with the one or moreelectrophiles.

During the polymerization at 904, one or more nitrogen atoms and/or aphosphorus atoms located in the one or more first type of amine monomersand the one or more second type of amine monomers can be subject toalkylation and/or quaternization; thus, the polymerization at 904 canconduct a polymer-forming reaction (e.g., formation of the copolymer)and an installation of charge (e.g., forming one or more first cations104 and/or one or more second cations 104) simultaneously without a needof a catalyst. Further, one or more hydrophobic functional groups 106can be derived from the one or more electrophiles and/or can be bondedto the one or more first cations 104 and/or the one or more secondcations 104 as a result of the alkylation and/or quaternization process.

For example, the copolymer formed at 904 can comprise a first ioneneunit 100 and/or a second ionene unit 100 and/or can be characterized byone or more embodiments of chemical formula 800. For instance, the firstionene unit 100 formed at 904 can comprise a molecular backbone 102 thatcan comprise one or more first cations 104 (e.g., represented by “X₁” inchemical formula 800), one or more first linkage groups (e.g.,represented by “L₁” in chemical formula 800), one or morebis(urea)guanidinium structures (e.g., as shown in FIG. 8), and/or oneor more hydrophobic functional groups 106 (e.g., represented by “R” inchemical formula 800). The one or more first cations 104 can be nitrogencations (e.g., protonated secondary amine cations, protonated tertiaryamine cations, quaternary ammonium cations, imidazolium cations, and/ora combination thereof) and/or phosphorus cations (e.g., quaternaryphosphonium cations). The one or more first cations 104 can be linked tothe one or more bis(urea)guanidinium structures via one or more firstlinkage groups (e.g., alkyl groups and/or aryl groups). Further, one ormore of the first cations 104 can be bonded to one or more of thehydrophobic functional groups 106. Additionally, the first ionene unit100 formed at 904 can repeat a number of times greater than or equal to1 and less than or equal to 1000.

The second ionene unit 100 formed at 904 can comprise a degradablemolecular backbone 102 that can comprise one or more second cations 104(e.g., represented by “X₂” in chemical formula 800), one or more secondlinkage groups (e.g., represented by “L₂” in chemical formula 800), oneor more terephthalamide structures (e.g., as shown in FIG. 8), and/orone or more hydrophobic functional groups 106 (e.g., represented by “R”in chemical formula 800). The one or more second cations 104 can benitrogen cations (e.g., protonated secondary amine cations, protonatedtertiary amine cations, quaternary ammonium cations, imidazoliumcations, and/or a combination thereof) and/or phosphorus cations (e.g.,quaternary phosphonium cations). The one or more second cations 104 canbe linked to the one or more terephthalamide structures via one or moresecond linkage groups (e.g., alkyl groups and/or aryl groups). Further,one or more of the second cations 104 can be bonded to one or more ofthe hydrophobic functional groups 106. Additionally, the second ioneneunit 100 formed at 904 can repeat a number of times greater than orequal to 1 and less than or equal to 1000. Additionally, one or morehydrophobic functional groups 106 can be bonded to both one or more ofthe first cations 104 (e.g., represented by “X₁” in FIG. 8) of the oneor more first ionene units 100 and one or more of the second cations 104(e.g., represented by “X₂” in FIG. 8) of the one or more second ioneneunits 100; thereby bonding the one or more first ionene units 100 withthe one or more second ionene units 100.

Antimicrobial activity of the one or more copolymers generated by themethod 900 can be independent of molecular weight. Thus, the method 900can target polymerization conditions that can extinguish molecularweight attainment by diffusion limited mechanism (e.g., polymerprecipitation) to modest molecular weights (e.g., molecular weights lessthan 7,000 g/mol), which can aid in the solubility of the repeatingionene units 100 in aqueous media.

FIG. 10A can illustrate an example, non-limiting scheme 1000 that candepict the generation of one or more copolymers (e.g., third ionenecomposition 1002, which can be characterized by chemical formula 800) inaccordance with one or more embodiments described herein (e.g., method900). Repetitive description of like elements employed in otherembodiments described herein is omitted for sake of brevity. Thus,scheme 1000 can depict a generation of one or more copolymers (e.g.,third ionene composition 1002 that can be characterized by chemicalformula 800) in accordance with the various features of method 900.While one or more particular amine monomers, electrophiles, and/orsolvents are depicted; additional embodiments of scheme 1000 are alsoenvisaged. For example, the principal mechanisms of scheme 1000 can beapplied to any amine monomer, electrophiles, and/or solvents inaccordance with the various features described herein (e.g., withreference to chemical formula 800 and/or method 900).

As shown in FIG. 10A, scheme 1000 can depict a polymerization (e.g., inaccordance with method 900) of one or more first monomers (e.g., firstamine monomer 402) and one or more second monomers (e.g., third aminemonomer 1004) with one or more electrophiles (e.g., p-xylylenedichloride) to generate one or more copolymers, which can be alternatingcopolymers and/or random copolymers (e.g., third ionene composition1002, which can be characterized by chemical formula 800). For example,the one or more first monomers (e.g., first amine monomer 402) and oneor more second monomers (e.g., third amine monomer 1004) can bedissolved with the one or more electrophiles (e.g., p-xylylenedichloride) in a solvent (e.g., DMF). The one or more first monomers(e.g., first amine monomer 402), the one or more second monomers (e.g.,third amine monomer 1004), the one or more electrophiles (e.g.,p-xylylene dichloride), and/or the solvent (e.g., DMF) can be stirred ata temperature greater than or equal to 15° C. and less than or equal to150° C. (e.g., 85° C.) for a period of time greater than or equal to 8hours and less than or equal to 72 hours (e.g., greater than or equal to12 hours and less than or equal to 24 hours).

The one or more copolymers (e.g., third ionene composition 1002, whichcan be characterized by chemical formula 800) can comprise a firstionene unit 100 and/or a second ionene unit 100. The first ionene unit100 can comprise a molecular backbone 102 having one or morebis(urea)guanidinium structures. A polymerization (e.g., thepolymerization at 904) can subject a functional group bonded to themolecular backbone 102 (e.g., first functional group 202 and/or secondfunctional group 204) to a quaternization with the one or moreelectrophiles; thereby bonding a hydrophobic group 106 to the molecularbackbone 102 and/or forming one or more first cations 104. For example,in scheme 1000, the quaternization can form one or more quaternaryammonium cations that can be bonded to both the molecular backbone 102(e.g., via a first linkage group) and the hydrophobic functional group106 (e.g., derived from the one or more electrophiles). Also, the firstionene unit 100 can repeat a number of times greater than or equal toone and less than or equal to one thousand.

The second ionene unit 100 can comprise a degradable (e.g.,biodegradable) molecular backbone 102 having one or more terephthalamidestructures. A polymerization (e.g., the polymerization at 904) cansubject a functional group bonded to the degradable molecular backbone102 to a quaternization with the one or more electrophiles; therebybonding a hydrophobic group 106 to the degradable molecular backbone 102and/or forming one or more second cations 104. For example, in scheme1000, the quaternization can form one or more quaternary ammoniumcations that can be bonded to both the degradable molecular backbone 102(e.g., via a second linkage group) and the hydrophobic functional group106 (e.g., derived from the one or more electrophiles). Also, the secondionene unit 100 can repeat a number of times greater than or equal toone and less than or equal to one thousand. In addition, one or more ofthe first cations 104 can be bonded to the same hydrophobic functionalgroup 106 as one or more of the second cations 104; thus, one or morecommon hydrophobic functional group 106 can bond the first ionene unit100 and the second ionene unit 100 together.

FIG. 10B can illustrate an example, non-limiting scheme 1006 that candepict the generation of one or more copolymers (e.g., fourth ionenecomposition 1008, which can be characterized by chemical formula 800) inaccordance with one or more embodiments described herein (e.g., method900). Repetitive description of like elements employed in otherembodiments described herein is omitted for sake of brevity. Thus,scheme 1006 can depict a generation of one or more copolymers (e.g.,fourth ionene composition 1008 that can be characterized by chemicalformula 800) in accordance with the various features of method 900.While one or more particular amine monomers, electrophiles, and/orsolvents are depicted; additional embodiments of scheme 1006 are alsoenvisaged. For example, the principal mechanisms of scheme 1006 can beapplied to any amine monomer, electrophiles, and/or solvents inaccordance with the various features described herein (e.g., withreference to chemical formula 800 and/or method 900).

As shown in FIG. 10B, scheme 1006 can depict a polymerization (e.g., inaccordance with method 900) of one or more first monomers (e.g., secondamine monomer 408) and one or more second monomers (e.g., fourth aminemonomer 1010) with one or more electrophiles (e.g., p-xylylenedichloride) to generate one or more copolymers, which can be alternatingcopolymers and/or random copolymers (e.g., fourth ionene composition1008, which can be characterized by chemical formula 800). For example,the one or more first monomers (e.g., second amine monomer 408) and oneor more second monomers (e.g., fourth amine monomer 1010) can bedissolved with the one or more electrophiles (e.g., p-xylylenedichloride) in a solvent (e.g., DMF). The one or more first monomers(e.g., second amine monomer 408), the one or more second monomers (e.g.,fourth amine monomer 1010), the one or more electrophiles (e.g.,p-xylylene dichloride), and/or the solvent (e.g., DMF) can be stirred ata temperature greater than or equal to 15° C. and less than or equal to150° C. (e.g., 85° C.) for a period of time greater than or equal to 8hours and less than or equal to 72 hours (e.g., greater than or equal to12 hours and less than or equal to 24 hours).

The one or more copolymers (e.g., fourth ionene composition 1008, whichcan be characterized by chemical formula 800) can comprise a firstionene unit 100 and/or a second ionene unit 100. The first ionene unit100 can comprise a molecular backbone 102 having one or morebis(urea)guanidinium structures. A polymerization (e.g., thepolymerization at 904) can subject a functional group bonded to themolecular backbone 102 (e.g., first functional group 202 and/or secondfunctional group 204) to an alkylation with the one or moreelectrophiles; thereby bonding a hydrophobic group 106 to the molecularbackbone 102 and/or forming one or more first cations 104. For example,in scheme 1006, the alkylation can form one or more imidazolium cationsthat can be bonded to both the molecular backbone 102 (e.g., via a firstlinkage group) and the hydrophobic functional group 106 (e.g., derivedfrom the one or more electrophiles). Also, the first ionene unit 100 canrepeat a number of times greater than or equal to one and less than orequal to one thousand.

The second ionene unit 100 can comprise a degradable (e.g.,biodegradable) molecular backbone 102 having one or more terephthalamidestructures. A polymerization (e.g., the polymerization at 904) cansubject a functional group bonded to the degradable molecular backbone102 to an alkylation with the one or more electrophiles; thereby bondinga hydrophobic group 106 to the degradable molecular backbone 102 and/orforming one or more second cations 104. For example, in scheme 1006, thealkylation can form one or more imidazolium cations that can be bondedto both the degradable molecular backbone 102 (e.g., via a secondlinkage group) and the hydrophobic functional group 106 (e.g., derivedfrom the one or more electrophiles). Also, the second ionene unit 100can repeat a number of times greater than or equal to one and less thanor equal to one thousand. In addition, one or more of the first cations104 can be bonded to the same hydrophobic functional group 106 as one ormore of the second cations 104; thus, one or more common hydrophobicfunctional group 106 can bond the first ionene unit 100 and the secondionene unit 100 together.

FIG. 11 illustrates a diagram of an example, non-limiting chemicalformula 1100 that can characterize the structure of an ionene unit 100in accordance with one or more embodiments described herein. Repetitivedescription of like elements employed in other embodiments describedherein is omitted for sake of brevity. In one or more embodiments, theionene unit 100 characterized by chemical formula 1100 can form amonomer. In various embodiments, a plurality of ionene units 100characterized by chemical formula 500 can be covalently bond together toform a polymer (e.g., an alternating copolymer and/or a randomcopolymer).

As shown in FIG. 11, an ionene unit 100 characterized by chemicalformula 1100 can comprise a degradable molecular backbone 102. Further,the degradable molecular backbone 102 can comprise a plurality ofbis(urea)guanidinium structures. In various embodiments, the ionene unit100 characterized by chemical formula 1100 can be derived from1,3-bis(butoxycarbonyl)guanidine, wherein the plurality of guanidiniumgroups can be derived from the 1,3-bis(butoxycarbonyl)guanidine.However, one or more embodiments of chemical formula 1100 can comprise aplurality of bis(urea)guanidinium structures derived from one or moremolecules other than 1,3-bis(butoxycarbonyl)guanidine.

The “X” in FIG. 11 can represent the one or more cations 104. Forexample, “X” can represent one or more cations 104 selected from a groupthat can include, but is not limited to: one or more nitrogen cations,one or more phosphorus cations, and/or a combination thereof. Forinstance, “X” can represent one or more nitrogen cations selected from agroup that can include, but is not limited to: one or more protonatedsecondary amine cations, one or more protonated tertiary amine cations,one or more quaternary ammonium cations, one or more imidazoliumcations, and/or a combination thereof. In another instance, “X” canrepresent one or more phosphorus cations selected from a group that caninclude, but is not limited to: one or more protonated secondaryphosphine cations, one or more protonated tertiary phosphine cations,one or more quaternary phosphonium cations, and/or a combinationthereof.

The one or more cations 104 (e.g., represented by “X” in chemicalformula 1100) can be covalently bonded to one or more linkage groups toform, at least a portion, of the degradable molecular backbone 102. Theone or more linkage groups can link the one or more cations 104 to theplurality of bis(urea)guanidinium structures, thereby comprising themolecular backbone 102. The “L” in FIG. 11 can represent the one or morelinkage groups. The one or more linkage groups can comprise anystructure in compliance with the various features of the molecularbackbone 102 described herein. For example, the one or more linkagegroups can have any desirable formation, including, but not limited to:chain formations, ring formations, and/or a combination thereof. The oneor more linkage groups can comprise one or more chemical structuresincluding, but not limited to: alkyl structures, aryl structures,alkenyl structures, aldehyde structures, ester structures, carboxylstructures, carbonyl structures, a combination thereof, and/or the like.For instance, “L” can represent one or more linkage groups that cancomprise an alkyl chain having greater than or equal to two carbon atomsand less than or equal to 15 carbon atoms.

As shown in FIG. 11, in various embodiments, an ionene unit 100characterized by chemical formula 1100 can comprise cations 104 (e.g.,represented by “X”) at a plurality of locations along the molecularbackbone 102. For example, cations 104 can be located at one or morecentral portions of the molecular backbone 102 (e.g., as shown in FIG.111). However, in one or more embodiments of chemical formula 1100, themolecular backbone 102 can comprise less or more cations 104 than thetwo illustrated in FIG. 11.

As shown in FIG. 11, “R₃” can represent a third functional group 1102covalently bonded to a plurality of the bis(urea)guanidium structures.One or more third functional group 1102 can comprise one or more estergroups and/or one or more carboxyl groups. For example, the thirdfunctional group 1102 can comprise one or more ester groups, which cancomprise one or more alkyl groups and/or one or more aryl groups. Thus,the third functional group 1102 can contribute degradability to themolecular backbone 102 of the one or more amine monomers characterizedby chemical formula 1100. Additionally, the third functional group 1102can facilitate in membrane targeting and control of hydrophobicityand/or hydrophilicity of the subject one or more amine monomers.

Further, the “R” shown in FIG. 11 can represent the one or morehydrophobic functional groups 106 in accordance with the variousembodiments described herein. For example, the one or more hydrophobicfunctional groups 106 can comprise one or more alkyl groups and/or oneor more aryl groups. For instance, the hydrophobic functional group 106can be derived from one or more dialkyl halides. The one or morehydrophobic functional groups 106 (e.g., represented by “R” in FIG. 11)can be covalently bonded to one or more of the cations 104 (e.g.,represented by “X” in FIG. 11) and/or the molecular backbone 102, whichcan comprise the one or more cations 104 (e.g., represented by “X” inFIG. 11), one or more linkage groups (e.g., represented by “L” in FIG.1), and/or a plurality of bis(urea)guanidinium structures.

FIG. 12 illustrates another flow diagram of an example, non-limitingmethod 1200 that can generate one or more ionene units 100, which can becharacterized by chemical formula 1100, in accordance with one or moreembodiments described herein. Repetitive description of like elementsemployed in other embodiments described herein is omitted for sake ofbrevity.

At 1202, the method 1200 can comprise dissolving one or more aminemonomers (e.g., characterized by chemical formula 200) with one or moreelectrophiles in a solvent. The one or more amine monomers (e.g.,characterized by chemical formula 200) can comprise a molecular backbone102 that has one or more bis(urea)guanidinium structures. The one ormore amine monomers can be degradable (e.g., biodegradable) and/orcomprise one or more functional groups (e.g., first functional group 202and/or second functional group 204). The first functional group 202 canbe an ester group and/or a carboxyl group. For example, the firstfunctional group 202 can comprise an ester group with an alkyl chainand/or aryl ring. The second functional group 204 can comprise an aminogroup and/or a phosphine group, either of which can be ionized to formone or more cations 104. The one or more amine monomers can furthercomprise a structure selected from a group that can include, but is notlimited to: alkyl amine groups, hetero cyclic amine groups, acombination thereof, and/or the like. For example, the one or more aminemonomers can be characterized by chemical formula 200 and/or generatedby method 400. In one or more embodiments, the one or more aminemonomers (e.g., characterized by chemical formula 200) can be preparedusing one or more techniques other than those described regarding method300.

The one or more electrophiles can comprise, for example, one or morealkyl halides (e.g., dialkyl halides). For instance, the one or moreelectrophiles can comprise one or more dialkyl halides having chlorideand/or bromide. Example electrophiles can include, but are not are notlimited to: p-xylylene dichloride, 4,4′-bis(chloromethyl)biphenyl;1,4-bis(bromomethyl)benzene; 4,4′-bis(bromomethyl)biphenyl;1,4-bis(iodomethyl)benzene; 1,6-dibromohexane; 1,8-dibromooctane;1,12-dibromododecane; 1,6-dichlorohexane; 1,8-dichlorooctane; acombination thereof; and/or the like.

The solvent can be an organic solvent. Additionally, the solvent can bean aprotic solvent, a dipolar solvent, and/or an alcohol. Examplesolvents can include but are not limited to: DMF, methanol, acombination thereof, and/or the like. For example, DMF can be used asthe solvent as it can dissolve the reactants at elevated temperatures.In one or more embodiments, equimolar amounts of the plurality ofdegradable amine monomers and the one or more electrophiles can bedissolved in the solvent.

To facilitate the dissolving at 1202, the method 1200 can optionallycomprise stirring the one or more amine monomers, the one or moreelectrophiles, and the solvent at a temperature greater than or equal to15° C. and less than or equal to 150° C. for a period of time greaterthan or equal to 8 hours and less than or equal to 72 hours (e.g.,greater than or equal to 12 hours and less than or equal to 24 hours).Additionally, an organocatalyst can optionally be added at 1202.Example, organocatalysts include, but are not limited to:1,8-diazabicyclo[5.4.0]undec-7-ene (“DBU”),1-(3,5-bis(trifluoromethyl)-phenyl)-3-cyclohexyl-2-thiourea (“TU”), acombination thereof, and/or the like.

At 1204, the method 1200 can comprise polymerizing the one or more aminemonomers and the one or more electrophiles to form an ionene unit 100.The ionene unit 100 (e.g., characterized by chemical formula 1100) cancomprise a cation 104 distributed along a degradable molecular backbone102. The molecular backbone 102 can comprise a plurality ofbis(urea)guanidinium structures (e.g., as illustrated in chemicalformula 1100). Further, the ionene unit 100 formed at 1104 can haveantimicrobial functionality and/or supramolecular assemblyfunctionality. In one or more embodiments, the polymerizing at 1104 canbe performed under nitrogen gas. Additionally, the polymerizing at 1104can generate the cation through alkylation and/or quaternation with theone or more electrophiles.

During the polymerization at 1104, a nitrogen atom and/or a phosphorusatom located in the one or more amine monomers (e.g., comprising thesecond functional group 204) can be subject to alkylation and/orquaternization; thus, the polymerization at 1104 can conduct apolymer-forming reaction (e.g., formation of the ionene unit 100) and aninstallation of charge (e.g., forming a cation 104, including a nitrogencation and/or a phosphorus cation) simultaneously without a need of acatalyst. Further, one or more hydrophobic functional groups 106 can bederived from the one or more electrophiles and/or can be bonded to theone or more cations 104 as a result of the alkylation and/orquaternization process.

The ionene unit 100 (e.g., characterized by chemical formula 1100)formed by method 1200 can be an ionene monomer. For example, thepolymerization at 1104 can bond two amine monomers (e.g., characterizedby chemical formula 200) together via one or more hydrophobic functionalgroups 106, wherein the second functional groups 204 of each aminemonomer are alkylized and/or quaternized with the one or moreelectrophiles to form one or more linkage groups, one or more cations104, and/or one or more hydrophobic functional groups 106. The firstfunctional groups 202 of the amine monomers can be ester groups and/orcarboxyl groups and thereby constitute the third functional groups 1102in the ionene unit 100 formed at 1204.

For example, the ionene formed at 1204 can comprise one or moreembodiments of the ionene unit 100 and can be characterized by one ormore embodiments of chemical formula 1100. For instance, the ionene unit100 formed at 1204 can comprise a degradable molecular backbone 102 thatcan comprise one or more cations 104 (e.g., represented by “X” inchemical formula 1100), one or more linkage groups (e.g., represented by“L” in chemical formula 1100), a plurality of bis(urea)guanidiniumstructures (e.g., as shown in FIG. 11), one or more hydrophobicfunctional groups 106 (e.g., represented by “R” in chemical formula1100), and/or one or more third functional groups 1102. The one or morecations 104 can be nitrogen cations (e.g., protonated secondary aminecations, protonated tertiary amine cations, quaternary ammonium cations,imidazolium cations, and/or a combination thereof) and/or phosphoruscations (e.g., quaternary phosphonium cations). The cations 104 can belinked to the plurality of bis(urea)guanidinium structures via one ormore linkage groups (e.g., alkyl groups and/or aryl groups). Further,one or more of the cations 104 can be bonded to one or more of thehydrophobic functional groups 106. Additionally, the one or more thirdfunctional groups 1102 can comprise one or more ester groups and/orcarboxyl groups, which can provide additional degradability to theionene unit 100.

Antimicrobial activity of the repeating ionene units 100 generated bythe methods described herein (e.g., method 1200) can be independent ofmolecular weight. Thus, the method 1200 can target polymerizationconditions that can extinguish molecular weight attainment by diffusionlimited mechanism (e.g., polymer precipitation) to modest molecularweights (e.g., molecular weights less than 7,000 g/mol), which can aidin the solubility of the repeating ionene units 100 in aqueous media.

FIG. 13 can illustrate an example, non-limiting scheme 1300 that candepict the generation of one or more ionene compositions (e.g., fifthionene composition 1302, which can be characterized by chemical formula1100) in accordance with one or more embodiments described herein (e.g.,method 1200). Repetitive description of like elements employed in otherembodiments described herein is omitted for sake of brevity. Thus,scheme 1300 can depict a generation of one or more ionene compositions(e.g., fifth ionene composition 1302 that can be characterized bychemical formula 1100) in accordance with the various features of method1200. While one or more particular amine monomers, electrophiles, and/orsolvents are depicted; additional embodiments of scheme 1300 are alsoenvisaged. For example, the principal mechanisms of scheme 1300 can beapplied to any amine monomer, electrophiles, and/or solvents inaccordance with the various features described herein (e.g., withreference to chemical formula 1100 and/or method 1200).

As shown in FIG. 13, scheme 1300 can depict a polymerization (e.g., inaccordance with method 1200) of one or more amine monomers (e.g., fifthamine monomer 1304) with one or more electrophiles (e.g., p-xylylenedichloride) to generate one or more ionene compositions (e.g., fifthionene composition 1302, which can be characterized by chemical formula1100). For example, fifth amine monomer 1304 can be characterized bychemical formula 200, wherein the first functional group 202 can be anester group comprising an first alkylation alkyl group and/or an arylgroup. The one or more amine monomers (e.g., fifth amine monomer 1304)can be dissolved with the one or more electrophiles (e.g., p-xylylenedichloride) in a solvent (e.g., DMF). The one or more amine monomers(e.g., fifth amine monomer 1304), the one or more electrophiles (e.g.,p-xylylene dichloride), and/or the solvent (e.g., DMF) can be stirred ata temperature greater than or equal to 15° C. and less than or equal to150° C. (e.g., 85° C.) for a period of time greater than or equal to 8hours and less than or equal to 72 hours (e.g., greater than or equal to12 hours and less than or equal to 24 hours).

The one or more ionene compositions (e.g., fifth ionene composition1302, which can be characterized by chemical formula 1100) can comprisea molecular backbone 102 having a plurality of bis(urea)guanidiniumstructures. A polymerization (e.g., the polymerization at 1204) cansubject a functional group bonded to the molecular backbone 102 of theone or more amine monomers (e.g., second functional group 204) to analkylation with the one or more electrophiles; thereby bonding ahydrophobic group 106 to the molecular backbone 102 and/or forming oneor more cations 104. For example, in scheme 1300, the alkylation canform one or more imidazole cations that can be bonded to both themolecular backbone 102 (e.g., via a linkage group) and the hydrophobicfunctional group 106 (e.g., derived from the one or more electrophiles).The one or more ionene compositions (e.g., fifth ionene composition1302) can comprise can be a monomer.

FIG. 14 illustrates a diagram of an example, non-limiting chart 1400that can depict the antimicrobial efficacy of one or more ionenecompositions in accordance with one or more embodiments describedherein. Repetitive description of like elements employed in otherembodiments described herein is omitted for sake of brevity. Todemonstrate the antimicrobial effects of the ionenes described herein(e.g., ionene units 100 that can be characterized by chemical formula200, 500, 800, and/or 1100 and/or generated by method 300, 600, 900,and/or 1200, such as those depicted in scheme 400, 700, 1000, and/or1300), a plurality of ionene compositions were evaluated against a broadspectrum of pathogens.

The first column 1402 of chart 1400 can depict the ionene compositionsubject to evaluation. The second column 1404 of chart 1400 can depictthe minimum inhibitory concentration (MIC) in micrograms per milliliter(μg/mL) of the subject ionene composition regarding Staphylococcusaureus (“SA”). The third column 1406 of chart 1400 can depict the MIC inμg/mL of the subject ionene composition regarding Escherichia coli(“EC”). The fourth column 1408 of chart 1400 can depict the MIC in μg/mLof the subject polyionene composition regarding Pseudomonas aeruginosa(“PA”). The fifth column 1410 of chart 1400 can depict the MIC in μg/mLof the subject polyionene composition regarding Candida albicans (“CA”).The sixth column 1412 of chart 1400 can depict the hemolytic activity(“HC₅₀”) in μg/mL of the subject polyionene composition regarding ratred blood cells.

FIG. 15 illustrates a diagram of an example, non-limiting graph 1500that can depict the hemolytic activity of various polyionenecompositions at various concentrations in accordance with the one ormore embodiments described herein. Repetitive description of likeelements employed in other embodiments described herein is omitted forsake of brevity. For example, FIG. 15 shows the hemolytic activity ofthe first ionene composition 702 (e.g., depicted by line 1502), thesecond ionene composition 706 (e.g., depicted by line 1504), the thirdionene composition 1002 (e.g., depicted by line 1506), and/or the fourthionene composition 1006 (e.g., depicted by line 1508) at concentrationsranging from 8 parts per million (ppm) to 2000 ppm. The hemolyticactivity depicted in graph 1500 can regard rat red blood cells. As shownin FIG. 15, the second ionene composition 706 and/or the third ionenecomposition 1002 have very similar hemolytic activity.

FIG. 16A illustrates a diagram of an example, non-limiting graph 1600that can depict the cell viability of the fifth ionene composition 1302.Repetitive description of like elements employed in other embodimentsdescribed herein is omitted for sake of brevity. Graph 1600 shows theviability of a L929 mouse fibroblast cell line after 48 hours ofincubation at 37° C. with the fifth ionene composition 1302 at variousconcentrations. Cell viability was determined through a3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT)assay.

FIG. 16B illustrates a diagram of an example, non-limiting graph 1602that can depict the hemolytic activity of various ionene compositions atvarious concentrations in accordance with the one or more embodimentsdescribed herein. Repetitive description of like elements employed inother embodiments described herein is omitted for sake of brevity. Forexample, graph 1602 can depict the hemolysis activity of the fifthionene composition 1302, and a sixth ionene composition. The sixthionene composition can be characterized by chemical formula:

wherein “n” can be an integer greater than or equal to one and less thanor equal to one thousand.

FIG. 17 illustrates another flow diagram of an example, non-limitingmethod 1700 of killing a pathogen, preventing the growth of a pathogen,and/or preventing contamination by a pathogen. Repetitive description oflike elements employed in other embodiments described herein is omittedfor sake of brevity. Example pathogens include, but are not limited to:Gram-negative bacteria, Gram-positive bacteria, fungi, yeast, acombination thereof, and/or the like.

At 1702, the method 1700 can comprise contacting the pathogen with achemical compound (e.g., an ionene, a polyionene, a monomer, and/or apolymer). The chemical compound can comprise an ionene unit 100 (e.g.,characterized by chemical formula 500, 800, and/or 1100). The ioneneunit 100 can comprise a cation 104 (e.g., a nitrogen cation cation)distributed along a degradable molecular backbone 102 that can compriseone or more bis(urea) structures (e.g., derived from1,3-bis(butoxycarbonyl)guanidine). The ionene unit 100 can haveantimicrobial functionality and/or supramolecular assemblyfunctionality.

At 1704, the method 1700 can comprise electrostatically disrupting amembrane of the pathogen (e.g., via lysis process 108) upon contactingthe pathogen with the chemical compound (e.g., an ionene unit 100characterized by chemical formula 500, 800, and/or 1100). Additionally,contacting the pathogen with the chemical compound (e.g., ionene unit100 characterized by chemical formula 500, 800, and/or 1100) can disruptthe membrane through hydrophobic membrane integration (e.g., via lysisprocess 108).

The ionene unit 100 that can comprise the chemical compound contactingthe pathogen at 1702 can comprise one or more embodiments of the ioneneunit 100 and can be characterized by one or more embodiments of chemicalformula 500, 800, and/or 1100. For instance, the ionene unit 100 cancomprise a molecular backbone 102 that can comprise one or more cations104 (e.g., represented by “X” in chemical formula 500, 800, and/or1100), one or more bis(urea)guanidinium structures (e.g., as shown inFIGS. 2, 4-5, 7-8, 10-11, and/or 13), one or more hydrophobic functionalgroups 106 (e.g., represented by “R” in chemical formula 500, 800,and/or 1100), and/or one or more functional groups to impart additionaldegradability (e.g., represented by R₃ in chemical formula 1100). Theone or more cations 104 can be nitrogen cations (e.g., quaternaryammonium cations, imidazolium cations, and/or a combination thereof)and/or phosphorus cations (e.g., quaternary phosphonium cations).Further, one or more of the cations 104 can be bonded to one or more ofthe hydrophobic functional groups 106. Additionally, the ionene unit 100can repeat a number of times greater than or equal to 1 and less than orequal to 1000. Therefore, the ionene unit 100 contacting the pathogen at1702 can comprise any and all the features of various embodimentsdescribed herein.

The various structures (e.g., described regarding FIGS. 1-2, 5, 8,and/or 11), compositions (e.g., described regarding FIGS. 4, 7, 10,and/or 13-16B), and/or methods (e.g., described regarding FIGS. 3, 6, 9,12, and/or 17) described herein can regard various chemical compoundsthat can be incorporated into a variety of applications. For example,said applications can include cleaning, sanitizing, disinfecting, and/orotherwise treating various articles such as, but not limited to: foodpackaging, medical devices, floor surfaces, furniture surfaces, woundcare instruments (e.g., bandages and/or gauss), building surfaces,plants (e.g., agricultural crops), ground surfaces, farming equipment,beds, sheets, clothes, blankets, shoes, doors, door frames, walls,ceilings, mattresses, light fixtures, facets, switches, sinks, grabrails, remote controls, vanities, computer equipment, carts, trolleys,hampers, bins, a combination thereof, and/or the like. In anotherexample, said applications can include pharmaceuticals, pharmaceuticalsalts, hygiene products (e.g., soaps and/or shampoos), and/or the like.In a further example, said applications can include agricultural spraysand/or aqueous solutions that can facilitate processing crops forconsumption.

In addition, the term “or” is intended to mean an inclusive “or” ratherthan an exclusive “or.” That is, unless specified otherwise, or clearfrom context, “X employs A or B” is intended to mean any of the naturalinclusive permutations. That is, if X employs A; X employs B; or Xemploys both A and B, then “X employs A or B” is satisfied under any ofthe foregoing instances. Moreover, articles “a” and “an” as used in thesubject specification and annexed drawings should generally be construedto mean “one or more” unless specified otherwise or clear from contextto be directed to a singular form. As used herein, the terms “example”and/or “exemplary” are utilized to mean serving as an example, instance,or illustration. For the avoidance of doubt, the subject matterdisclosed herein is not limited by such examples. In addition, anyaspect or design described herein as an “example” and/or “exemplary” isnot necessarily to be construed as preferred or advantageous over otheraspects or designs, nor is it meant to preclude equivalent exemplarystructures and techniques known to those of ordinary skill in the art.

What has been described above include mere examples of systems,compositions, and methods. It is, of course, not possible to describeevery conceivable combination of reagents, products, solvents, and/orarticles for purposes of describing this disclosure, but one of ordinaryskill in the art can recognize that many further combinations andpermutations of this disclosure are possible. Furthermore, to the extentthat the terms “includes,” “has,” “possesses,” and the like are used inthe detailed description, claims, appendices and drawings such terms areintended to be inclusive in a manner similar to the term “comprising” as“comprising” is interpreted when employed as a transitional word in aclaim. The descriptions of the various embodiments have been presentedfor purposes of illustration, but are not intended to be exhaustive orlimited to the embodiments disclosed. Many modifications and variationswill be apparent to those of ordinary skill in the art without departingfrom the scope and spirit of the described embodiments. The terminologyused herein was chosen to best explain the principles of theembodiments, the practical application or technical improvement overtechnologies found in the marketplace, or to enable others of ordinaryskill in the art to understand the embodiments disclosed herein.

What is claimed is:
 1. A monomer comprising: a molecular backbonecomprising a bis(urea)guanidinium structure covalently bonded to afunctional group comprising a radical, and wherein the monomer hassupramolecular assembly functionality.
 2. The monomer of claim 1,wherein the functional group is selected from a group consisting of anamino group, a phosphine group and an ester group.
 3. The monomer ofclaim 2, wherein the functional group is the amino group, and whereinthe amino group is selected from another group consisting of a tertiaryamino group, an imidazole group and a heterocycle group.
 4. The monomerof claim 1, wherein the monomer has a structure characterized byformula:

wherein R₁ represents a second functional group and is selected from afirst group consisting of a first amino group, a first phosphine groupand an ester group; and wherein R₂ represents the functional group andis selected from a second group consisting of a second amino group and asecond phosphine group.
 5. The monomer of claim 4, wherein the secondfunctional group is the first amino group and is selected from a thirdgroup consisting of a first tertiary amino group and a first imidazolegroup; and wherein the second functional group is the second amino groupand is selected from a fourth group consisting of a second tertiaryamino group and a second imidazole group.
 6. The monomer of claim 4,wherein the second functional group is the ester group, and wherein thefunctional group is the second amino group and is selected from a thirdgroup consisting of a tertiary amino group and an imidazole group.
 7. Achemical compound comprising: an ionene unit comprising a cationdistributed along a degradable backbone, the degradable backbonecomprising a bis(urea)guanidinium structure, wherein the ionene unit hasantimicrobial functionality.
 8. The chemical compound of claim 7,wherein the cation is selected from a group consisting of a nitrogencation and a phosphorus cation.
 9. The chemical compound of claim 7,wherein the cation is a nitrogen cation selected from a second groupconsisting of a protonated secondary amine cation, a protonated tertiaryamine cation, a quaternary ammonium cation and an imidazolium cation.10. The chemical compound of claim 7, wherein the cation is covalentlybonded to a hydrophobic functional group.
 11. The chemical compound ofclaim 10, wherein the ionene unit has a structure characterized byformula 1:

wherein X₁ represents the cation, wherein R represents the hydrophobicfunctional group, wherein n represents an integer greater than or equalto one and less than or equal to one thousand, and wherein L₁ representsa linkage group selected from a second group consisting of an alkylgroup and an aryl group.
 12. The chemical compound of claim 11, whereinthe cation is a nitrogen cation selected from a third group consistingof a protonated secondary amine cation, a protonated tertiary aminecation, a quaternary ammonium cation and an imidazolium cation.
 13. Thechemical compound of claim 11, wherein the chemical compound furthercomprises a second ionene unit covalently bonded to the ionene unit,wherein the chemical compound has another structure characterized byformula 2:

wherein X₂ represents a second cation, wherein m represents a secondinteger greater than or equal to one and less than or equal to onethousand, and wherein L₂ represents a second linkage group selected froma third group consisting of a second alkyl group and a second arylgroup.
 14. The chemical compound of claim 7, wherein the ionene unit hasa structure characterized by formula 1:

wherein R₁ represents an ester group, wherein X represents the cation,wherein R₂ represents a hydrophobic functional group, and wherein Lrepresents a linkage group selected from a group consisting of an alkylgroup and an aryl group.
 15. A method comprising: aminolyzing an estergroup of a monomer with an aminolysis reagent, the monomer comprisingthe ester group covalently bonded to a guanidinium group, wherein theaminolyzing forms a molecular backbone comprising a bis(urea)guanidiniumstructure.
 16. The method of claim 15, further comprising: dissolvingthe monomer and the aminolysis reagent in a solvent to form a solution;and stirring the solution at a temperature greater than or equal to 15degrees Celsius (° C.) and less than or equal to 150° C. for a period oftime greater than or equal to 8 hours and less than or equal to 72hours.
 17. The method of claim 16, wherein the aminolysis reagent is adiamine comprising a first amino group and a second amino group; whereinthe first amino group selected from a first group consisting of a firstprimary amino group and a first secondary amino group; and wherein thesecond amino group selected from a second group consisting of a secondprimary amino group, a second secondary amino group, a tertiary aminogroup and an imidazole group.
 18. A method comprising: dissolving anamine monomer with an electrophile in a solvent, the amine monomercomprising a molecular backbone, and the molecular backbone comprising abis(urea)guanidinium structure; and polymerizing the amine monomer andthe electrophile to form an ionene unit, the ionene unit comprising acation located along the molecular backbone, wherein the ionene unit hasantimicrobial functionality.
 19. The method of claim 18, furthercomprising: stirring the amine monomer, the electrophile, and thesolvent at a temperature greater than or equal to 15 degrees Celsius (°C.) and less than or equal to 150° C. for a period of time greater thanor equal to 8 hours and less than or equal to 72 hours.
 20. The methodof claim 19, wherein the polymerizing comprises a process to form thecation, and wherein the process is selected from a group consisting ofan alkylation and a quaternization.
 21. The method of claim 20, whereinthe electrophile is a dialkyl halide, wherein the solvent is an organicsolvent, and wherein the cation is a nitrogen cation selected from afirst group consisting of a protonated secondary amine cation, aprotonated tertiary amine cation, a quaternary ammonium cation and animidazolium cation.
 22. A method comprising: dissolving a first aminemonomer, a second amine monomer, and an electrophile in solvent, thefirst amine monomer comprising a molecular backbone, the molecularbackbone comprising a bis(urea)guanidinium structure, the second aminemonomer comprising a degradable backbone, and the degradable backbonecomprising a terephthalamide structure; and polymerizing the first aminemonomer and the second amine monomer with the electrophile to form acopolymer, the copolymer comprising a first cation distributed along themolecular backbone and a second cation distributed along the degradablebackbone, wherein the copolymer has antimicrobial functionality.
 23. Themethod of claim 22, further comprising: stirring the first aminemonomer, the second amine monomer, the electrophile, and the solvent ata temperature greater than or equal to 15 degrees Celsius (° C.) andless than or equal to 150° C. for a period of time greater than or equalto 8 hours and less than or equal to 72 hours.
 24. The method of claim23, wherein the polymerizing comprises a first process to form the firstcation; wherein the first process is selected from a first groupconsisting of a first alkylation and a first quaternization; wherein thepolymerizing comprises a second process to form the second cation;wherein the second process is selected from a second group consisting ofa second alkylation and a second quaternization.
 25. The method of claim24, wherein the electrophile is a dialkyl halide; wherein the solvent isan organic solvent; wherein the first cation is a first nitrogen cationselected from a third group consisting of a first protonated secondaryamine cation, a first protonated tertiary amine cation, a firstquaternary ammonium cation and a first imidazolium cation; and whereinthe second cation is a second nitrogen cation selected from a fourthgroup consisting of a second protonated secondary amine cation, a secondprotonated tertiary amine cation, a second quaternary ammonium cationand a second imidazolium cation.